38966-21-1 Usage
Description
APHIDICOLIN, also known as (+)-Aphidicolin, is a naturally occurring tetracyclic diterpene with potent antiviral, antimitotic, and antibiotic properties. It is a cell-permeable compound first isolated from the fungus C. aphidicola and has shown activity against various viruses, including herpes simplex. APHIDICOLIN acts as a reversible inhibitor of DNA replication by specifically targeting DNA polymerases α, δ, and ε in eukaryotic cells and some animal viruses. It is also known to induce apoptosis, prolong the half-life of DNA methyltransferase, and exhibit synergistic effects with certain antitumor agents.
Uses
Used in Antiviral Applications:
APHIDICOLIN is used as an antiviral agent for its activity against herpes simplex and other viruses. It inhibits viral replication by blocking the activity of specific DNA polymerases, making it a valuable tool in the study and treatment of viral infections.
Used in Antimitotic Applications:
APHIDICOLIN is used as an antimitotic agent for its ability to block the cell cycle at the early S-phase. This property makes it useful in synchronizing cell division and as a research tool in cell differentiation studies.
Used in Apoptosis Induction:
APHIDICOLIN is used as an apoptosis inducer in leukemia cell lines and HeLaS3 cells. It potentiates apoptosis induced by arabinosyl nucleosides and has been shown to act synergistically with antitumor agents such as vincristine and doxorubicin.
Used in DNA Polymerase Inhibition:
APHIDICOLIN is used as a specific inhibitor of DNA polymerase α and δ in eukaryotic cells. It blocks the cell cycle at the early S-phase, making it a valuable tool in the study of DNA replication and cell cycle regulation.
Used in Parasitic Infections:
APHIDICOLIN is used as an active agent against Leishmania parasites, providing a potential therapeutic option for the treatment of leishmaniasis.
Used in Cancer Research:
APHIDICOLIN is used as a research tool in cancer studies due to its ability to arrest cells in the G1/S phase and increase gene amplification frequency. This property aids in understanding the mechanisms of cell cycle regulation and the development of targeted cancer therapies.
Used in Pharmaceutical Industry:
APHIDICOLIN is used as a cell synchronization agent in the pharmaceutical industry for its ability to block the cell cycle at the early S-phase, facilitating the study of cell division and differentiation.
Used in Research and Development:
APHIDICOLIN is used as a research tool in various scientific fields, including virology, cell biology, and cancer research, due to its diverse biological activities and potential applications in the development of new therapeutic strategies.
Biochem/physiol Actions
Cell permeable: yes
References
1) Syvaoja et al. (1990), DNA polymerases alpha, delta, and epsilon: three distinct enzymes from HeLa cells; Proc. Natl. Acad. Sci. USA, 87 6664
2) Urbani et al. (1995), Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization; Exp. Cell Res., 219 159
3) Kuwakado et al. (1993), Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines; Biochem. Pharmacol., 46 1909
4) Yin and Schimke (1996), Inhibition of apoptosis by overexpressing Bcl-2 enhances gene amplification by a mechanism independent of aphidicolin pretreatment; Proc. Natl. Acad. Sci. USA, 93 3394
Check Digit Verification of cas no
The CAS Registry Mumber 38966-21-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,8,9,6 and 6 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 38966-21:
(7*3)+(6*8)+(5*9)+(4*6)+(3*6)+(2*2)+(1*1)=161
161 % 10 = 1
So 38966-21-1 is a valid CAS Registry Number.
InChI:InChI=1/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
38966-21-1Relevant articles and documents
A New End Game for Aphidicolin
Rizzo, Carmelo J.,Smith, Amos B.
, p. 2793 - 2796 (1988)
A highly efficient, stereocontrolled synthesis of aphidicolin from its degradation product, 3α,18-isopropylidenedioxy-17-noraphidicolan-16-one, has been achieved.
The hydroxylation at C-17 in the biosynthesis of the diterpenoid aphidicolin
Hanson, James R.,Hitchcock, Peter B.,Jarvis, Andrew G.
, p. 1055 - 1059 (2007/10/03)
The hydroxylation at C-17 in aphidicolin biosynthesis is inhibited by a 17-thiol. A metabolite hydroxylated at C-17 and retaining the cyclopropane ring was obtained from 3α,18-dihydroxy-15β,16β-methanoaphidicolane whilst aphidicolin itself was obtained from 3α,18-dihydroxyaphidicolane when these substrates were incubated with the fungus, Cephalosporium aphidicola.
Rearrangements of the C/D Ring System of the Tetracyclic Diterpenoid, Aphidicolin
Hanson, James R.,Hitchcock, Peter B.,Jarvis, Andrew G.,Ratcliffe, Arnold H.
, p. 1773 - 1778 (2007/10/02)
The generation of a C-16 carbocation in the aphidicolane series by the hydrolysis of a 15β,16β- or a 16β,17-epoxide is shown to lead, inter alia, to skeletal rearrangement products arising from the migration of the C(12)-C(13) bond to C-16.
